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20th September 2016 @ 05:49

 

AEW 205 (500 mg, 1.96 mmol, 1 equiv) was suspended in anhydrous toluene (10 mL) along with potassium hydroxide (384 mg, 6.84 mmol, 3.5 equiv) and 18-crown-6 (36 mg, 0.14 mmol, 0.07 equiv). AEW 287-2 (435 mg, 0.67 mmol, 1 equiv) was dissolved in anhydrous toluene and added to the reaction mixture whilst stirring at rt for ten mins. Reaction heated to 40 ˚C with stirring.

After 1h, still SM

EtOAc 1 h.jpeg

The sample was cooled to room temperature and diluted with 10 mL of water. The mixture was extracted with EtOAc (3 x 20 mL). The combined organic layer was washed with water (1 x 10 mL) until the aqueous layer became neutral followed by brine (6 mL) and dried over Na2SO4. The orange/yellow fluoro solution was filtered and dried under reduced pressure and in vacuo to yield an orange oil that was dried at the high vac.

 

Data:


InChi:

InChI=1S/C11H9ClF2N4O/c1-7(3-2-4-19-11(13)14)10-17-16-9-6-15-5-8(12)18(9)10/h2-3,5-6,11H,1,4H2/b3-2-

and

InChI=1S/C13H18O3/c14-10-12(11-6-2-1-3-7-11)16-13-8-4-5-9-15-13/h1-3,6-7,12-14H,4-5,8-10H2

to

InChI=1S/C25H24F2N4O4/c26-25(27)34-19-11-9-18(10-12-19)24-30-29-21-14-28-15-22(31(21)24)33-16-20(17-6-2-1-3-7-17)35-23-8-4-5-13-32-23/h1-3,6-7,9-12,14-15,20,23,25H,4-5,8,13,16H2


ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

and

OCC(OC1OCCCC1)C2=CC=CC=C2

to

FC(F)OC(C=C1)=CC=C1C2=NN=C3N2C(OCC(OC4OCCCC4)C5=CC=CC=C5)=CN=C3

Attached Files
EtOAc 1 h.jpeg
AEW 232-3.rxn
AEW 232-3.cdx
AEW 232-3.png